Process of making vanillin, &amp;c.



UNITED srA'rEs PATENT OFFICE.

EDWARD (J. SPURGE, OF NIAGARA FALLS, NEW YORK, ASSIGNOR TO OZONE VANILLIN COMPANY, A CORPORATION OF NEWXORK Specification of Letters Patent.

Patented Aug. 21, 1906.

Application filed November 2], 1905. Serial Ho. 288.873-

.[0 all whom it may concern.-

Be it known that I, EDWARD CnAnLns SPURGE, a subject of the King of England, residing in Niagara Falls, New York, have invented new and useful Im rovements in Processes of Obtaining Vanillm and Similar Bodies; and in order that others skilled in the art to which my invention belongs may understand and practice the same I give the following specification.

My invention relates to a rocess for Ohtaining vanillin and similar y-constituted substances from carbon compounds which are characterized by a benzene nucleus with alateral chain, (0,11 Such carbon compounds mayhave a lateral chain either in the form CH CH OH or its isomer OH CH CH,. The carbon compound to which I particularly refer is isoeugenol. Heretofore it has been proposed to treat such compounds suspended in water or in the form of a solution with ozone or ozonized air, which by its reaction upon the compound converts the same into the corresponding aldeyhde as for, instance, by the treatment of isoeu eno in the manner stated the aldehyde vanifiin is produced. It has been found in ractice that this process results in a considerable waste of material and a relatively small old 'of the vanillin, and, further, that relatively large masses of material are required to be handled to obtain a relatively small proportion of the aldehyde.

I have discovered that the relatively low 'eld and otherunfavol'ableresults obtained ythe above process, particularlyin the case 0 vanillin, are due in large measure to the formation and presence of a resinous bed of unknown composition which is reduce in the reaction. This resinous bo y causes a thickening of the reaction mass and the aldehyde formed coagulates' or agglomerates therein until as the reaction progresses this thickening and ag lomeration reaches a oint where the 0x1 izin action is seriously interfered with and impaired and the further production of vanillin materially diminished.

It is the object of the invention to provide means for preventing the thickening and agglomeration referred to and to maintain the reaction mass in a relatively thin fluid condition and most favorable to the thorou h oxidation of the carbon compound.

have discovered that if certain salts be added to the fluid to be treated the producr tion of the resinous body is very considerably diminished, the thickening'of the mass prevented, and a more fluid condition thereof is maintained which is favorable to the oxidation process the obtaining of increased eld. For this purpose a bisulfite salt may h e added in the form of a solution and the mass treated with ozone.

The vanillin formed combines with the bisulfite, either wholly or partially with the formation of a bisulfite compound which goes into solution either wholly or artiall according to the quantity of bisul te emp oyed. That ortion which forms the bisulfite compoun is less thick and more fluid and acts in the manner of an emulsifyin medium. During the reaction there is li erated an amount of S0,, and a certain amount of neutral sulfite and sulfate are formed. The latter, particulafillly the sulfate, being less soluble than thegbis te are precipitated in a state of fine division during the oxidation process and being disseminated throughout the mass act favorably therein in keeping the same in a state of fine subdivision. stood that d the oxidation rocess the ozonized air is b own through tl ie reaction mass and the same is thereby kept in a 'tation. The bisulfite to be employed may e a bisulfite of an alkali. Preferably I employ bisuifite of soda. 7

For the purposes of illustration I give the following example of my invention as applied to isoeugenol: To one hundred poun s of isoe nol are added three hundred pounds of so 'um bisulfite of about 36 Baum. The mass is charged into a suitable receiver to which is connected a sup ly of ozone or the mass for a length of time sufficient to carry the oxidation to the desired degree. The skilled operator will readily determine the de es of oxidation suited to the character oft e product he desires, the character of the ozonized air-that is, its proportion of ozone, &c.- These conditions varyin practice, and the skilled operator will determine the proper length of time required to complete the gliocess; In the process illustrated the vanil' formed is recovered and separated from the mass in any of the well-known It will be under-.

ozonized air, and the latter 18 passed throughwa s.

ther carbon compounds of the character describedfor instance, iso-safrol and the like-may be treated according to my invention with good results.

Having thus described my invention, the following is what I claim as new therein and desire to secure by Letters Patent:

1. The process of oxidizing a carbon compound having a benzene nucleus with a lateral chain (1 H to produce the correspondin aldehyde, which consists in treating said compound in admixture with a solution of an acid salt of sulfurous acid with ozone or ozonized air.

2. The process of oxidizing a carbon compound havin a benzene nucleus with a lateral chain (IS-I to produce the corresponding aldehyde, which consists in treating said com ound in admixture with a solution of an alkai hisulfite with ozone or ozonized air.

3. The process of producing vanillin, which consists in adding to a quantity of isoeuge- 1101 a proportion of bisulfite solution, and subjecting said mixture to the action of ozone or ozonized air.

4. The process of producing vanillin, which consists in adding to a quantity of isoeugenol a proportion of a solution of sodium bisulfite of about 36 Baum and treating the mixture with ozone or ozonized air EDWARD C. SPURGE. 

